Podcast Summary: All There Is with Anderson Cooper

Episode: Ben Stiller: Facing His Past
Date: December 10, 2025
Host: Anderson Cooper
Guest: Ben Stiller

Episode Overview

In this emotionally raw episode, Anderson Cooper sits down with actor, writer, and director Ben Stiller to explore the many layers of grief, memory, and family legacy. The conversation is set against the backdrop of Stiller’s documentary film, "Stiller and Nothing is Lost," which chronicles his journey sorting through his late parents’ belongings. Anderson and Ben share their parallel experiences of loss, the struggle to face their pasts, the cyclical nature of grief, perfectionism inherited from their parents, and the ongoing challenge of breaking familial patterns.
The episode is honest, confessional, frequently humorous, and threaded with insight relevant to anyone navigating grief or family history.

Key Discussion Points & Insights

1. The Timelessness and Evolution of Grief

(00:33–02:18)

• Anderson begins by playing a listener voicemail from Grace, who lost her mother to suicide five years prior. Grace expresses frustration with people insisting that a particular year is always "the hardest" and worries about when—if ever—grief gets easier.
  • Quote – Grace (00:33):
    "Every year at least one person has told me that the year I'm in is the hardest year … What year is the easiest? When will I have the easiest year? And I really hope I haven't already had it."
• Anderson reflects on how others’ attempts to categorize or timeline grief can feel invalidating, sharing Nick Cave’s wisdom:
  • Quote – Nick Cave (02:41):
    "There was some years, or a year at least, of absolute, devastating, incapacitating sorrow … You think that it’s simply unbearable, and you learn ultimately that actually it’s not. You can bear it."

2. Confronting the Past Through Belongings

(03:35–07:36)

• Ben Stiller describes starting to go through his parents’ things almost immediately after his father’s passing in 2020, driven by a sense of panic as the apartment felt like "home base."
  • Quote – Ben Stiller (04:13):
    "It was kind of like this knee-jerk react of, like, I just, I'm not gonna remember this place fully. I wanna just film it so I can."
• Stiller discovered an unexpected treasure trove of cassette recordings, including family moments and old sketch improvisations—each item or artifact triggering deep memories or new revelations.
• Anderson empathizes, having amassed untouched boxes in his own basement, and both relate to the overwhelming, sometimes Sisyphean, nature of sorting through a lifetime of belongings.

3. Memories, Artifacts, and Emotional Weight

(06:01–09:31)

• Stiller reflects on artifacts like old glasses and suitcases, imbuing intensely personal meaning to mundane objects.
  • Quote – Ben Stiller (06:17):
    "They're part of your parents … There's something just very heavy about that, too."
• Both men reminisce about growing up amidst New York’s quirky 1970s scene, peppered with household parties, famous guests, and family rituals.

4. Making Sense of Upbringing and Patterns

(09:31–12:51)

• Anderson ponders the effort to make sense of growing up in a storied family, saturated with sensory impressions and cultural icons.
• The discussion turns to the risk of unconsciously repeating their parents’ patterns—especially the prioritization of work over family—and the challenge of self-awareness.
  • Quote – Ben Stiller (12:03):
    "What happened is like my relationship with my work became very important to me and probably like out of balance with really attending to all the relationships in my life."

5. Perfectionism, Legacy, and Generational Repetition

(12:51–17:48)

• Perfectionism emerges as a defining trait on both sides; both Anderson and Ben describe its isolating, sometimes joyless, consequences.
• In a raw audio excerpt from Stiller’s parents, his mother laments her husband’s inability to enjoy their successes because of his relentless striving.
  • Quote – Ann Meara (17:48):
    "It is joyless. Absolutely joyless."

6. Active Grieving and Emotional Openness

(19:18–24:33)

• Anderson and Ben discuss whether they have truly grieved their parents, recognizing a shared tendency to keep up "deflector shields."
• Stiller shares a spiritual moment of feeling his mother's presence while at her old boarding school, underscoring how subtle triggers can evoke meaningful connections with the departed.

7. Learning How to Grieve

(23:52–25:51)

• Anderson admits he spent his life suppressing grief, until pursuing conversations with others helped him learn about grieving as an active, multidimensional process.
  • Quote – Anderson Cooper (23:29):
    "I need to actually grieve. I need to actually feel, allow myself to feel … and it’s been life changing."
• He cites lessons from Stephen Colbert and Francis Weller: grief as a gift, and the idea that one's relationship with the dead can continue to evolve.

8. Newfound Empathy, Acceptance, and Connection

(24:33–26:06)

• Stiller describes how sorting through family history increased his appreciation of his parents and built unexpected bonds with others experiencing similar loss.
  • Quote – Ben Stiller (25:51):
    "The understanding a little bit more what it is to be a person, and … I feel better. I feel a little better about all of it, you know, like, because it’s out in the open."

9. Societal Constraints on Grief Conversations

(26:06–28:34)

• Both men lament how open dialogue about loss or death remains taboo on television and in society.
• Anderson points out how even fleeting public acknowledgments of grief (like his annual New Year’s Eve comments) evoke enormous gratitude from viewers who feel seen.

10. Regrets and Mortality

(28:34–31:15)

• Stiller shares discomfort at hearing old tapes where his parents express sadness over his emotional distance; now, as a parent of adult children, he sympathizes with both sides.
• Stiller discusses his prostate cancer diagnosis and how confronting mortality brought bouts of gratitude and new perspective on the fragility of life.

Notable Quotes & Memorable Moments

• Grace (Listener, 00:33): "What year is the easiest? When will I have the easiest year?"
• Nick Cave (02:41): "You think that it’s simply unbearable, and you learn ultimately that actually it’s not. You can bear it. And all sorts of extraordinary things happen within this thing that we call grief."
• Ben Stiller (04:13): "[After my dad died] it was kind of like this knee-jerk react of, like, I just, I'm not gonna remember this place fully. I wanna just film it so I can."
• Ben Stiller (06:17): "They're part of your parents. I don't know. There's something just very heavy about that, too."
• Anderson Cooper (09:31): "I'm trying to make sense of what happened. Like, what was this entire experience of growing up in the family that I grew up in ... saturated with colors and the smell of Rigo candles and cigarettes and clinking glasses and people drinking."
• Ben Stiller (12:03): "What happened is like my relationship with my work became very important to me and probably like out of balance with really attending to all the relationships in my life."
• Ann Meara (Ben's mother, 17:48): "It is joyless. Absolutely joyless."
• Anderson Cooper (23:29): "I need to actually grieve. I need to actually feel, allow myself to feel … and it’s been life changing."
• Ben Stiller (24:33): "The people who are really close to you and that have made an impact and are a part of you ... those relationships go on and continue."
• Ben Stiller (25:51): "I feel better. I feel a little better about all of it, you know, like, because it’s out in the open."
• Ben Stiller (30:02): "When you get a diagnosis like that, everything stops ... all of it’s like, wait a minute, this is something that could change everything."

Timestamps for Important Segments

• 00:33: Listener "Grace" shares her experience of long-term grief and the recurring expectation of when it will “get easier.”
• 02:41: Nick Cave’s philosophy on the endurance of grief.
• 04:13: Ben Stiller describes the urgent instinct to document his parents’ apartment and possessions right after losing his father.
• 06:17: The power of physical objects as memory triggers.
• 12:03: Admitting to repeating parents’ work-centric patterns, unintentionally sidelining relationships.
• 14:14–15:22: Ben’s conversation with his own son, directly confronting the effects of his absence.
• 17:48: Ann Meara's candid assessment of her husband’s perfectionism ("It is joyless. Absolutely joyless.").
• 23:29: Anderson’s realization about the need to actively grieve after discovering his late father’s essay.
• 24:33: Ongoing relationships with loved ones after loss.
• 30:02: Facing mortality: Ben Stiller on learning he had prostate cancer.

Conclusion & Takeaways

This intimate, searching conversation deconstructs the myths and expectations around grief, revealing its long, unpredictable, and deeply personal journey. Anderson Cooper and Ben Stiller find kinship in their struggles—and discover, through both humor and heartbreak, that active remembrance, candid conversation, and the courage to face emotional pain are the foundations for healing.
Their stories affirm: Grief is not a problem to solve, but a relationship to nurture—one that can, with time and honesty, grow richer and more generous.

For further engagement:

• Ben Stiller's film "Stiller and Mira: Nothing is Lost" is streaming on Apple TV.
• To share your own story or connect with others, visit the "All There Is" community at cnn.com/allthereis.